1-Cyclo-hexyl-methyl-3-methyl-2-[(phenyl-imino)(sulfido)meth-yl]benzimidazolium.

In the zwitterionic title compound, C(22)H(25)N(3)S, the benzimid-azole ring system makes a dihedral angle of 55.69 (11)° with the phenyl ring. In the crystal structure, inter- and intra-molecular C-H⋯S inter-actions occur.

Related literature

For related structures, see: Öztürk et al. (2004 ▶); Akkurt et al. (2005 ▶). For background, see: Allen et al. (1987 ▶); Cremer & Pople (1975 ▶); Küçükbay et al. (1995 ▶); Winberg & Coffman (1965 ▶).

Experimental

Crystal data

C22H25N3S

M = 363.52

Monoclinic,

a = 11.0999 (8) Å

b = 12.4601 (7) Å

c = 15.0143 (14) Å

β = 99.007 (7)°

V = 2051.0 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.17 mm−1

T = 296 K

0.62 × 0.56 × 0.51 mm

Data collection

Stoe IPDSII diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.903, T max = 0.919

11769 measured reflections

3997 independent reflections

2727 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.127

S = 1.02

3997 reflections

236 parameters

H-atom parameters constrained

Δρmax = 0.36 e Å−3

Δρmin = −0.37 e Å−3

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808008842/hb2714sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808008842/hb2714Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C22H25N3S	F000 = 776
Mr = 363.52	Dx = 1.177 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 12543 reflections
a = 11.0999 (8) Å	θ = 1.4–28.0º
b = 12.4601 (7) Å	µ = 0.17 mm−1
c = 15.0143 (14) Å	T = 296 K
β = 99.007 (7)º	Block, yellow
V = 2051.0 (3) Å3	0.62 × 0.56 × 0.51 mm
Z = 4

Stoe IPDSII diffractometer	3997 independent reflections
Monochromator: plane graphite	2727 reflections with I > 2σ(I)
Detector resolution: 6.67 pixels mm-1	Rint = 0.031
T = 296 K	θmax = 26.0º
ω scans	θmin = 1.9º
Absorption correction: integration(X-RED32; Stoe & Cie, 2002)	h = −13→13
Tmin = 0.903, Tmax = 0.919	k = −15→13
11769 measured reflections	l = −18→18

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.046	H-atom parameters constrained
wR(F2) = 0.127	w = 1/[σ2(Fo2) + (0.0746P)2] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
3997 reflections	Δρmax = 0.36 e Å−3
236 parameters	Δρmin = −0.37 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
S1	0.40319 (5)	0.79425 (5)	0.26689 (5)	0.0886 (2)
N1	0.28968 (12)	0.63297 (12)	0.44357 (9)	0.0502 (5)
N2	0.34915 (12)	0.54355 (11)	0.33351 (9)	0.0487 (4)
N3	0.16469 (13)	0.75498 (13)	0.28359 (10)	0.0572 (5)
C1	0.32300 (14)	0.53150 (14)	0.47690 (11)	0.0503 (6)
C2	0.32500 (17)	0.48719 (19)	0.56177 (13)	0.0650 (7)
C3	0.36543 (19)	0.3831 (2)	0.57255 (16)	0.0738 (8)
C4	0.40346 (18)	0.32577 (18)	0.50294 (17)	0.0738 (8)
C5	0.40103 (17)	0.36931 (16)	0.41825 (15)	0.0632 (7)
C6	0.36035 (14)	0.47437 (14)	0.40713 (12)	0.0494 (5)
C7	0.30640 (14)	0.63806 (14)	0.35726 (11)	0.0465 (5)
C8	0.2483 (2)	0.72060 (18)	0.49579 (14)	0.0687 (7)
C9	0.27958 (15)	0.73442 (14)	0.29906 (11)	0.0507 (5)
C10	0.11976 (17)	0.84557 (17)	0.23179 (13)	0.0614 (6)
C11	0.1515 (2)	0.94910 (19)	0.25693 (16)	0.0791 (8)
C12	0.0936 (3)	1.0351 (2)	0.2082 (2)	0.1043 (11)
C13	0.0082 (3)	1.0155 (4)	0.1341 (3)	0.1179 (14)
C14	−0.0228 (3)	0.9139 (4)	0.1091 (2)	0.1084 (13)
C15	0.03093 (19)	0.8291 (2)	0.15829 (15)	0.0815 (9)
C16	0.38428 (16)	0.51876 (17)	0.24565 (12)	0.0577 (6)
C17	0.27793 (17)	0.49794 (17)	0.17240 (12)	0.0612 (7)
C18	0.3246 (2)	0.4812 (2)	0.08393 (14)	0.0816 (9)
C19	0.2221 (3)	0.4596 (3)	0.00661 (17)	0.1112 (15)
C20	0.1411 (3)	0.3698 (3)	0.02668 (19)	0.1048 (11)
C21	0.0958 (3)	0.3852 (3)	0.1148 (2)	0.1050 (11)
C22	0.2009 (2)	0.4028 (2)	0.19119 (16)	0.0819 (9)
H2	0.30040	0.52580	0.60880	0.0780*
H3	0.36730	0.35010	0.62830	0.0890*
H4	0.43140	0.25590	0.51360	0.0890*
H5	0.42530	0.33040	0.37130	0.0760*
H8A	0.25970	0.78770	0.46680	0.0830*
H8B	0.29450	0.72060	0.55540	0.0830*
H8C	0.16330	0.71110	0.49940	0.0830*
H11	0.21140	0.96190	0.30640	0.0950*
H12	0.11300	1.10520	0.22600	0.1250*
H13	−0.02890	1.07270	0.10060	0.1410*
H14	−0.08080	0.90140	0.05830	0.1300*
H15	0.00700	0.75950	0.14170	0.0980*
H16A	0.43660	0.45600	0.25200	0.0690*
H16B	0.43130	0.57830	0.22750	0.0690*
H17	0.22580	0.56180	0.16650	0.0730*
H18A	0.38080	0.42110	0.08990	0.0980*
H18B	0.36900	0.54460	0.07030	0.0980*
H19A	0.17360	0.52420	−0.00590	0.1330*
H19B	0.25680	0.44200	−0.04700	0.1330*
H20A	0.18580	0.30280	0.02830	0.1260*
H20B	0.07190	0.36490	−0.02140	0.1260*
H21A	0.04980	0.32240	0.12770	0.1260*
H21B	0.04160	0.44660	0.11050	0.1260*
H22A	0.16900	0.41490	0.24690	0.0980*
H22B	0.25140	0.33890	0.19880	0.0980*

	U11	U22	U33	U12	U13	U23
S1	0.0631 (3)	0.0819 (4)	0.1212 (5)	−0.0041 (3)	0.0155 (3)	0.0461 (4)
N1	0.0531 (7)	0.0518 (9)	0.0451 (8)	−0.0037 (6)	0.0063 (6)	0.0022 (7)
N2	0.0498 (7)	0.0496 (8)	0.0461 (8)	0.0028 (6)	0.0061 (6)	0.0030 (6)
N3	0.0568 (8)	0.0579 (9)	0.0562 (9)	0.0096 (7)	0.0069 (7)	0.0065 (7)
C1	0.0478 (8)	0.0543 (11)	0.0468 (10)	−0.0099 (7)	0.0015 (7)	0.0064 (8)
C2	0.0643 (11)	0.0787 (14)	0.0501 (11)	−0.0184 (10)	0.0035 (8)	0.0113 (10)
C3	0.0692 (12)	0.0802 (16)	0.0676 (13)	−0.0205 (11)	−0.0033 (10)	0.0307 (12)
C4	0.0626 (11)	0.0596 (12)	0.0941 (17)	−0.0073 (9)	−0.0038 (11)	0.0271 (12)
C5	0.0598 (10)	0.0516 (11)	0.0762 (13)	−0.0010 (8)	0.0049 (9)	0.0094 (10)
C6	0.0446 (8)	0.0500 (10)	0.0515 (10)	−0.0047 (7)	0.0008 (7)	0.0094 (8)
C7	0.0443 (8)	0.0503 (10)	0.0441 (9)	−0.0025 (7)	0.0047 (6)	0.0023 (7)
C8	0.0832 (13)	0.0683 (14)	0.0568 (11)	0.0026 (10)	0.0175 (9)	−0.0095 (10)
C9	0.0565 (9)	0.0501 (10)	0.0443 (9)	0.0013 (7)	0.0044 (7)	0.0030 (8)
C10	0.0633 (10)	0.0690 (13)	0.0535 (10)	0.0197 (9)	0.0143 (8)	0.0077 (10)
C11	0.1043 (16)	0.0682 (15)	0.0667 (13)	0.0194 (12)	0.0196 (12)	0.0080 (11)
C12	0.133 (2)	0.0744 (17)	0.117 (2)	0.0412 (16)	0.055 (2)	0.0263 (16)
C13	0.110 (2)	0.147 (3)	0.104 (2)	0.073 (2)	0.0394 (18)	0.062 (2)
C14	0.0856 (17)	0.159 (3)	0.0791 (17)	0.052 (2)	0.0083 (13)	0.029 (2)
C15	0.0686 (12)	0.1101 (19)	0.0644 (13)	0.0266 (12)	0.0061 (10)	0.0061 (13)
C16	0.0604 (10)	0.0609 (12)	0.0541 (10)	0.0051 (8)	0.0165 (8)	0.0017 (9)
C17	0.0694 (11)	0.0609 (12)	0.0528 (11)	0.0152 (9)	0.0077 (8)	−0.0019 (9)
C18	0.1018 (16)	0.0905 (17)	0.0537 (12)	0.0079 (13)	0.0156 (11)	0.0038 (12)
C19	0.141 (3)	0.133 (3)	0.0545 (14)	0.023 (2)	−0.0003 (15)	0.0003 (15)
C20	0.114 (2)	0.105 (2)	0.0840 (18)	0.0193 (17)	−0.0204 (16)	−0.0297 (16)
C21	0.0878 (16)	0.127 (2)	0.0957 (19)	−0.0097 (15)	0.0007 (14)	−0.0336 (18)
C22	0.0780 (14)	0.0992 (18)	0.0685 (14)	−0.0149 (12)	0.0116 (11)	−0.0101 (13)

S1—C9	1.6968 (18)	C20—C21	1.500 (4)
N1—C1	1.388 (2)	C21—C22	1.518 (4)
N1—C7	1.339 (2)	C2—H2	0.9300
N1—C8	1.460 (3)	C3—H3	0.9300
N2—C6	1.392 (2)	C4—H4	0.9300
N2—C7	1.339 (2)	C5—H5	0.9300
N2—C16	1.466 (2)	C8—H8A	0.9600
N3—C9	1.286 (2)	C8—H8B	0.9600
N3—C10	1.416 (3)	C8—H8C	0.9600
C1—C2	1.386 (3)	C11—H11	0.9300
C1—C6	1.383 (2)	C12—H12	0.9300
C2—C3	1.374 (3)	C13—H13	0.9300
C3—C4	1.385 (3)	C14—H14	0.9300
C4—C5	1.379 (3)	C15—H15	0.9300
C5—C6	1.386 (3)	C16—H16A	0.9700
C7—C9	1.487 (2)	C16—H16B	0.9700
C10—C11	1.374 (3)	C17—H17	0.9800
C10—C15	1.375 (3)	C18—H18A	0.9700
C11—C12	1.396 (4)	C18—H18B	0.9700
C12—C13	1.366 (5)	C19—H19A	0.9700
C13—C14	1.350 (7)	C19—H19B	0.9700
C14—C15	1.371 (5)	C20—H20A	0.9700
C16—C17	1.505 (3)	C20—H20B	0.9700
C17—C18	1.514 (3)	C21—H21A	0.9700
C17—C22	1.514 (3)	C21—H21B	0.9700
C18—C19	1.517 (4)	C22—H22A	0.9700
C19—C20	1.495 (5)	C22—H22B	0.9700
C1—N1—C7	108.81 (14)	N1—C8—H8B	110.00
C1—N1—C8	125.17 (14)	N1—C8—H8C	109.00
C7—N1—C8	125.97 (15)	H8A—C8—H8B	110.00
C6—N2—C7	108.94 (14)	H8A—C8—H8C	109.00
C6—N2—C16	125.52 (15)	H8B—C8—H8C	109.00
C7—N2—C16	125.48 (15)	C10—C11—H11	120.00
C9—N3—C10	120.80 (16)	C12—C11—H11	120.00
N1—C1—C2	131.24 (17)	C11—C12—H12	120.00
N1—C1—C6	106.88 (14)	C13—C12—H12	120.00
C2—C1—C6	121.87 (17)	C12—C13—H13	120.00
C1—C2—C3	116.26 (19)	C14—C13—H13	120.00
C2—C3—C4	122.0 (2)	C13—C14—H14	120.00
C3—C4—C5	121.9 (2)	C15—C14—H14	120.00
C4—C5—C6	116.21 (19)	C10—C15—H15	120.00
N2—C6—C1	106.42 (15)	C14—C15—H15	120.00
N2—C6—C5	131.86 (17)	N2—C16—H16A	109.00
C1—C6—C5	121.70 (17)	N2—C16—H16B	109.00
N1—C7—N2	108.95 (15)	C17—C16—H16A	109.00
N1—C7—C9	124.16 (15)	C17—C16—H16B	109.00
N2—C7—C9	126.89 (15)	H16A—C16—H16B	108.00
S1—C9—N3	133.19 (14)	C16—C17—H17	108.00
S1—C9—C7	115.18 (12)	C18—C17—H17	108.00
N3—C9—C7	111.63 (15)	C22—C17—H17	108.00
N3—C10—C11	122.96 (18)	C17—C18—H18A	109.00
N3—C10—C15	117.92 (19)	C17—C18—H18B	109.00
C11—C10—C15	118.8 (2)	C19—C18—H18A	109.00
C10—C11—C12	120.0 (2)	C19—C18—H18B	109.00
C11—C12—C13	119.6 (3)	H18A—C18—H18B	108.00
C12—C13—C14	120.6 (4)	C18—C19—H19A	109.00
C13—C14—C15	120.2 (3)	C18—C19—H19B	109.00
C10—C15—C14	120.9 (3)	C20—C19—H19A	109.00
N2—C16—C17	113.91 (15)	C20—C19—H19B	109.00
C16—C17—C18	109.15 (16)	H19A—C19—H19B	108.00
C16—C17—C22	113.59 (17)	C19—C20—H20A	109.00
C18—C17—C22	109.66 (18)	C19—C20—H20B	109.00
C17—C18—C19	112.2 (2)	C21—C20—H20A	109.00
C18—C19—C20	112.4 (2)	C21—C20—H20B	109.00
C19—C20—C21	112.2 (3)	H20A—C20—H20B	108.00
C20—C21—C22	111.2 (3)	C20—C21—H21A	109.00
C17—C22—C21	111.2 (2)	C20—C21—H21B	109.00
C1—C2—H2	122.00	C22—C21—H21A	109.00
C3—C2—H2	122.00	C22—C21—H21B	109.00
C2—C3—H3	119.00	H21A—C21—H21B	108.00
C4—C3—H3	119.00	C17—C22—H22A	109.00
C3—C4—H4	119.00	C17—C22—H22B	109.00
C5—C4—H4	119.00	C21—C22—H22A	109.00
C4—C5—H5	122.00	C21—C22—H22B	109.00
C6—C5—H5	122.00	H22A—C22—H22B	108.00
N1—C8—H8A	109.00
C7—N1—C1—C2	178.50 (18)	C1—C2—C3—C4	0.7 (3)
C8—N1—C1—C2	0.9 (3)	C2—C3—C4—C5	−1.1 (3)
C7—N1—C1—C6	−0.28 (18)	C3—C4—C5—C6	1.1 (3)
C8—N1—C1—C6	−177.88 (16)	C4—C5—C6—C1	−0.8 (3)
C1—N1—C7—N2	0.09 (19)	C4—C5—C6—N2	177.97 (18)
C8—N1—C7—N2	177.66 (16)	N2—C7—C9—N3	112.86 (19)
C1—N1—C7—C9	179.56 (15)	N1—C7—C9—S1	113.46 (16)
C8—N1—C7—C9	−2.9 (3)	N1—C7—C9—N3	−66.5 (2)
C6—N2—C7—N1	0.14 (18)	N2—C7—C9—S1	−67.2 (2)
C16—N2—C7—N1	−177.02 (15)	N3—C10—C11—C12	−172.9 (2)
C6—N2—C7—C9	−179.31 (15)	C11—C10—C15—C14	1.9 (3)
C16—N2—C7—C9	3.5 (3)	C15—C10—C11—C12	0.2 (3)
C6—N2—C16—C17	105.6 (2)	N3—C10—C15—C14	175.3 (2)
C7—N2—C16—C17	−77.7 (2)	C10—C11—C12—C13	−2.0 (4)
C7—N2—C6—C5	−179.20 (18)	C11—C12—C13—C14	1.7 (5)
C7—N2—C6—C1	−0.31 (18)	C12—C13—C14—C15	0.3 (5)
C16—N2—C6—C1	176.85 (15)	C13—C14—C15—C10	−2.2 (4)
C16—N2—C6—C5	−2.0 (3)	N2—C16—C17—C18	176.01 (17)
C9—N3—C10—C11	−61.4 (3)	N2—C16—C17—C22	−61.3 (2)
C9—N3—C10—C15	125.6 (2)	C16—C17—C18—C19	180.0 (2)
C10—N3—C9—S1	−2.0 (3)	C22—C17—C18—C19	54.9 (3)
C10—N3—C9—C7	178.02 (15)	C16—C17—C22—C21	−179.6 (2)
N1—C1—C6—N2	0.36 (18)	C18—C17—C22—C21	−57.1 (3)
C6—C1—C2—C3	−0.4 (3)	C17—C18—C19—C20	−52.9 (3)
N1—C1—C2—C3	−179.03 (18)	C18—C19—C20—C21	52.0 (4)
N1—C1—C6—C5	179.38 (16)	C19—C20—C21—C22	−54.1 (4)
C2—C1—C6—N2	−178.56 (16)	C20—C21—C22—C17	57.1 (3)
C2—C1—C6—C5	0.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16A···S1i	0.97	2.73	3.683 (2)	167
C16—H16B···S1	0.97	2.78	3.451 (2)	127

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16A⋯S1i	0.97	2.73	3.683 (2)	167
C16—H16B⋯S1	0.97	2.78	3.451 (2)	127

Symmetry code: (i) .